My Boyfriend is a Better Sister

She smiled and looked at me, "What size?"

I snickered, "Oh, they aren't for me. They are for him. Tell her what size."

As the clerk gave us that surprised look, Carl cleared his throat, "Size nine."

We went back to the ladies shoe department and the employee brought out a couple of boxes with low heels and I quickly informed her, "I think he is looking for something a little higher. Maybe a three inch heel?" I looked at Carl, "Do agree?"

He somberly agreed, "Yeah."

When the clerk returned with 4 boxes of high heels, we were in business. One box contained a pair of 4 inch stilettos which I quickly disregarded because he would never be able to walk in those and I didn't want to be cruel.

I lifted a pair of red three inch strappy heels from the box and displayed them, "These are similar to what you were wearing yesterday. These might work." I looked at the worker and asked, "Ma'am can he try these on?"

Carl sat down and slid his shoes off showing his freshly painted toes glistening the through the clear nylon. Without saying a word, she knelt and strapped the heels on Carl. He stood up and walked around to see if they would fit him correctly. They were a good fit but the color seemed not right.

Carl asked, "Do these come in any other colors?"

I was so proud because he had asked a question and I added to his question, "I agree. The color might not work with his toes. I think black would work better."

She pulled out a pair of three inch black office pumps with a slight opened toe front and presented, "I have some in the back. Before I get them, perhaps you might like these? Not only are they stylish, they are practical. I have a pair at home and I can wear them for hours before they hurt my feet."

After Carl tried them on and walked around, we had found his pair. They were perfect. We purchased them before heading to our next venue which was the clothing store. At our third store, we saw some amazing dresses that we suspected would fit. After sorting through the racks and holding up some of them in front of him to eye judge if they fit, I settled on 5 that he would try on.

I pointed to another young female employee and instructed Carl, "See if she can open up the dressing room so you can try these on."

From a distance, I saw Carl ask the girl and she immediately came over with him to unlock the door while telling me, "Those are nice choices. I think you will like how they fit."

Once again I had to correct a worker, "I'm sorry. They are not for me. He will be the one trying them on."

She laughed because she thought I was joking before realizing, "Oh, you're serious? I apologize. Of course, here you go."

I stepped in and watched Carl try on all the dresses. A couple of them had the wrong fit and one was the wrong color. I needed something that was sexy but not too revealing because we were attempting to pass Carl off as a girl without anyone knowing. We found a black and silver shimmer cocktail dress that we liked and it had a nice fit. It had long sleeves which we needed and it came down to his mid-thigh. He could wear the black stockings and pumps and look very sexy without exposing he was actually male. I also picked up two large silicone bra inserts along with a pair of flesh colored crotchless spanx to keep his junk sucked in as well as shaping him to be a little more feminine. I would have him wear them backwards so the opening would be in the back.

We stopped and had his eyebrows plucked, his ears pierced and purchased a short blond, inward bobbed wig with bangs. Our shopping was over and with bags in hand, we headed back to my place. We were ready for Carl's makeover to transform him into Carla. Federico was home and was excited to help me.

Carl showered and came out ready. Federico and I had to do a great job in transforming Carl so that his cover would not be blown. We first fit him with the panties and bra, including the inserts which gave him nice B cup boobs. Our next job was makeup. Federico applied Carl's foundation while I worked on his eyes. I added some fake lashes before the liner. I then put on his eye shadow and the smoky bronze I chose made his eyes pop. Federico carefully applied his lipstick. When we were finished, Federico snapped his fingers, "Child, he has features I would die for. I think we can pull this off."

It was now time to get Carl dressed. Federico helped him put on the black stockings with the elastic lace to hold them up while I fitted him with his spanx, bra and panties. We both slipped his dress on so not to mess up his makeup and Federico did wonders with the wig. Our final touch was the jewelry and after we were finished, we were astonished at our work.

Federico sarcastically claimed, "Girlfriend, he is prettier that you are."

I laughed and felt a sense of accomplishment that Carl was transformed into a pretty girl named Carla. I also knew we had to be realistic and not think that everyone would think he was female if we didn't take some precautions. I already had his legs covered in nylon and his arms covered with sleeves. The place we were going needed to be dimly lit and even though we practiced his higher speaking voice, he would need to limit speaking at all.

I was dressed similar to Carl in that I was wearing a form fitting cocktail dress with the exact strappy high heels that I caught Carl wearing. I left my hair down but spiral curled it and wore my long silver earrings. I had an idea of where we would go. It was a country bar about 40 miles away with a live band. I was only 20 but had an authentic fake ID and borrowed my real sister's ID for Carl. The bar had a reputation of being a rougher, rowdy crowd but as two ladies, I felt we would be safe as long as we kept up the ruse. I went over the rules a few times with Carl as we drove to the establishment. It was a pleasant evening with a full moon.

We arrived and parked in the front. We were both a little nervous when we walked in so we quickly found a table towards the back. We were overdressed but turned heads. The band's music was playing and in no time, some drinks were sent to us by a businessman wearing a suit, sitting at the bar. We waved our thanks and talked among each other. As we scanned the entire place, we could see there were some rougher looking people but overall, it wasn't terrible. Couples were dancing and most were having a great time.

I knew people thought Carl was actually a female. One guy ask him to dance but he panicked and respectfully declined. Finally, when two big biker men dressed in leather with thick beards and several tattoos, sitting back by the bathroom, ordered us drinks, I knew it was time to make our move.

I walked over to their table when the largest one slurred, "Well honey, I'm glad you came to your senses and came over here to some real men. How would you like to go a few rounds with us?"

With several empty shot glasses sitting on the table, I could tell they were drunk which I felt would work in our favor when I giggled, "I think we might take you up on that." I pointed over to Carl dressed as Carla and began my lie, "Do you see the blonde girl over there wearing the black dress? She is my sister and just found out her boyfriend cheated on her. She is very shy and doesn't speak much but she wants to get even with that prick and told me that she wanted to go out back with you two and have a little fun. What do you think?"

The other biker laughed, "I say fuck an A but we are on our hogs. How about you two get on with us and we go to the nearest hotel?"

Just then another guy with a cowboy hat, long mustache, and wearing cowboy boots, sitting beside them on the end bar stool, interrupted our conversation, "I'm sorry guys but I couldn't help but overhearing you and if you let me in on this, I have a large U-Haul truck parked in the back. I just got in from Texas. My wife and I are moving here and still have some furniture inside, including a nice couch. I'm Leroy by the way."

The bikers looked at each other and agreed before one of them introduced themselves, "Partner, I think you have yourselves a fuckin deal. I'm Ace and that is George."

I said, "Great. Let me go talk to my sister and we will meet you in the back."

The three men walked out the back door together. I told Carl that they were his chance to prove he could pull off being a girl and satisfy my wishes and his urges. He disagreed and really didn't want to go through with it but I convinced him otherwise. We walked out back just in time to see Cowboy Leroy raise the back door of his large truck. As we walked under the moonlight and a dull nearby streetlight we watched him move a couple of boxes off the couch.

Leroy popped out, pulled the ramp down and offered, "There you go little ladies. I will wait out here and make sure nobody comes by."

Carl and I walked up the ramp and got inside before the two bikers followed. Ace was about 6'4 and 270 pounds while George was smaller at 6'1 and 240 but still a large man. Both guys looked to be in their late 30s.

Ace stumbled once before crashing down on the couch then slurred, "We gonna fuck or what?"

I said in a seductive voice, "We are going to give you guys the best blowjobs you have ever had. I'm on my monthly and we just want to make you guys feel good."

George swayed and unbuttoned his leather pants, "Shit, yeah. I can go for that." Then he grabbed Carl and planted a huge, open mouthed kissed on him confirming that George really thought he was a girl.

I helped Ace stand back up, yank his leather pants down and his white underwear, allowing his cock to flop out. George was able to get his pants down by himself and then they both crashed back down on the couch side by side. The inside of the trailer now reeked of alcohol. Using the cushions from a separate love seat, Carl and I were able to have a knee rest. It isn't easy squatting down in form fitting dresses, but we managed. Both of us began sucking our own man. At one point, I could see that Carl's head was dipping up and down in unison with mine.

Both bikers were groaning in ecstasy when George's large hand took the back of Carl's head and forced him down deeper on his seven inches, "I want you to take it all, Bitch. God damn...keep sucking my fuckin dick!"

Ace was more laid back and allowed me to gulp his thicker seven inches while he leaned back on the couch with his hands connected behind his head. His beard was so long, I could feel it ticking my forehead every time I went down on his cock.

George warned Carl in his gravelly voice, "I'm cummin! Ungh...ungh...ungh...yeah...ungh! Stay down! That's it, stay down!"

George pressed Carl's head all the way down on his meat while he blasted his cum down Carl's throat. Carl was gagging and coughing, trying to take George's sperm as it painted his tonsils.

When George stopped cumming, he released Carl's head before he suffocated and offered, "There you go baby. That is some top notch gravy right there. I need another shot."

Almost pushing Carl out of the way, George stood and pulled his pants up. Carl was left on his knees swallowing George's cum. Now the truck trailer not only smelled of alcohol, it stunk of sweaty leather and semen.

George was buckling his belt when he stepped out of the truck and proclaimed to Leroy who was still standing guard, "She is one good cocksucker. Get in there and get ya some of that mouth when Ace is done."

I was still sucking Ace's dick when I lifted my head and suggested to Carl, "Carla, I think you should finish off Ace. You are doing so well and you can get even with that bastard ex-boyfriend of yours."

I stood up, pulled my short dress back down and allowed Carl to take my place as Ace slurred, "Get on it girl. I'm gonna blow the back of your head off with this."

With now smeared lipstick, Carl started sucking Ace for all he was worth. Ace's dirty boot covered feet straightened out as he relaxed even more. Ace was drunker than George, so he was taking longer to cum and Carl added his hand to jerk while he sucked.

Leroy yelled a loud whisper into the truck trailer, "Hey! Somebody is coming!"

Ace snapped back, "Damn right somebody is gonna cum. That person is me!"

Just then I heard a stranger's voice next to Leroy ask, "Is everything OK? Do you guys need help?"

Ace yelled out of the truck with a loud echo, "Get the fuck out of here or wait your turn, man! Can't you see I'm getting my dick sucked in here? Do you mind?"

The stranger grumbled and walked off but Carl never stopped blowing Ace even while the conversation was taking place. Carl's pace increased and Ace was getting closer.

Ace then gasped when his cock began to spurt into the sucking mouth of Carl, "Here it comes! Here it comes! Oh shit, there it is! Ahhh! Aughhhh, there it is! Oh fuck, take that shit! Augghhhh!" Even after Ace was finished, Carl continued sucking until Ace pushed him off, "That's enough baby. It's sensitive."

Ace pulled up, then zipped up. As he walked out he bellowed to Leroy, "She's all yours. Damn! That was some good ass head. My Old Lady hasn't done that in years."

While Carl was swallowing Ace's deposit, I whispered, "I think it's time. Bend over the couch and let him do you in ass. I think we need to find out if you like that."

Carl began to panic, "I don't think so. He will know I'm a guy dressed like this and he will kill us."

I reassured, "It's gonna be fine. I will take care of it. Get up and bend over the arm of the couch and just pull your dress up over your butt. It is very dark in here and he has been drinking. Trust me. Hurry, here he comes."

Carl got off his knees, shimmied his dress up before bending over the arm and placing his hands on the cushion where Ace was sitting. Even in the darkness, I could see clearly the tops of his stockings and the opening in his panties. It would be the perfect distraction and entrance for the cowboy.

Leroy chuckled, "You ready for me ladies?"

I chimed in with another lie as he arrived, "Carla still wants to get even with her ex-boyfriend who cheated on her. He was always bragging how he was the only one who ever had anal sex with her. She wants you to do her in the ass. What do you say to that?"

"I say, hell yeah! My Old Lady has never done that," agreed the excited Leroy as he copied Ace's remark.

In my clutch purse, I had a small tube of Vaseline for my lips. I unsnapped it and showed the tube to Cowboy Leroy, "Let me lube you up baby."

Leroy was also a smaller guy as he only stood a couple inches taller than Carl but when he yanked his jeans down, out flopped a huge dong causing me to gasp, "Oh...my...God!"

Sensing I was worried for his virgin ass, Carl who was still bent over and couldn't see Leroy, quickly asked, "Oh my God, what?"

I wanted to ease his mind, "Uh...nothing. Just relax and take it Carla. I know you can do it."

Leroy stooped down and began kissing "Carla's" crotchless panty covered ass. He also stuck his finger inside the top of "her" black stockings. When his cock swelled to its full strength, it was so massive that it looked fake.

I didn't have the heart to tell Carl that Leroy was about to put a horse sized nine inch, thick dick in his asshole. Instead, I wanted to make sure I greased it up thoroughly. I used the entire tube of Vaseline on that thing and smeared it around evenly. I even stuck a huge glob on Carl's sphincter and twisted a couple fingers inside while he squirmed.

With his jeans down around his knees overtop his cowboy boots and still wearing his cowboy hat, Leroy asked Carla, "You ready for me baby?"

Carl could see the fear in my eyes so therefore I could see the fear in his. I sat down on the couch by his downward facing head, squeezed his hand before comforting, "Carla, look at me. It's going to be OK. Just relax your butthole and welcome it in. When the pressure builds in the beginning, clench really tight then relax. Repeat that over and over."

By that time, Leroy already had his fist sized cock head pinned up against Carl's opening. He pushed and when it popped inside, Carl let out a whimper that echoed throughout the truck.

"Ouch...ouch...ouch! It's not going to fit," Carl yelped in his high voice.

I rubbed his hand and soothed, "It will. Give it time. Your rectum will stretch and get used to it. Breathe. That's it, breathe."

Carl was breathing heavily with his lipstick smeared lips pressed together in kiss blowing formation. Leroy was clutching onto Carl's hips and slowly feeding his ass more and more of his inches. I was proud of Carl because it didn't take Leroy long to have all nine inches buried all the way to his balls.

Carl was squeezing my hand like a woman trying to give birth. He was gritting his teeth and thrashing his head. Meanwhile, Cowboy Leroy was starting to thrust in and out. I had to see this, even if it was just in a glimmer of dim light. I stood up and peeked around Carl's leg. There it was, that massive slippery dick, sliding in and out of his rectum like it was meant to be there.

Soon, I could tell the pain was starting to subside and transform into pleasure. The spongy head of Leroy's penis must have been rubbing Carl's prostate because he was not grimacing as much. He put his head down and took what Leroy had to offer like a good little slut.

Leroy was grunting, "You are so tight. You are going to make me cum pretty soon. I love how you can take all of it darlin"

As Leroy pounded Carl's tight ass, the high heels Carl was wearing were sliding on the metal floor, causing him to lean too far forward. To compensate, Leroy allowed Carl to put his knees up on the arm of the couch. Cowboy Leroy increased his pace, jarring Carl so much that those high heels fell off, one at a time, on the floor so that his stocking covered feet were hanging over. Carl was squealing as Leroy got closer to orgasm.

"You ready baby? Here it comes!" Leroy warned before erupting, "Ah, damn! I'm cummin! Ah! Ah! Take it, all! Fuck I'm still squirtin! Hang on! Augghh! There we go!"

When Leroy finished cumming he just stood there winded while clutching Carl's hips. After a minute, he slowly withdrew his large cock from Carl's ass before pulling his pants up.

While adjusting his shirt, he expressed his gratitude, "Thank ya darlin. When any girl, including my wife, sees how big this thing is, they won't let me go near their ass. Thank ya again."

With a butt full of cum, Carl stood up and adjusted his dress back down to its normal position. He found and slipped his pumps back on before we walked down the ramp and back into the bar. We both went to the ladies room so he could wipe up the cum and we could adjust our lipstick. We then decided to leave. When we got back to my place, we were exhausted. I helped him remove his makeup and we slept in the same bed as sisters.

The next morning, I was fixing breakfast when Carl walked out. He had a serious look on his face and had me sit down before explaining, "I think you are right. After last night, I have all these feelings about who I am and who I'm supposed to be. Last night was so raw and so amazing, I came in my pants just from the thrill. We can't stay together and I want to thank you for exposing that in me. Last night was so exciting and I finally felt like my true self. I love you so much for doing that."

We parted ways and he ended up leaving school. I later saw on social media that he was actually transforming into a female. I felt proud to have helped her find her true self.